The macromonomer means a compound that can be regarded as a high molecular weight monomer (usually several hundreds to ten thousands in molecular weight) that contains a polymerizable functional group on one terminal end of the molecule. It was first proposed by Milkovich et al. of U.S.A. in 1972 (cf. U.S. Pat. No. 3,786,116 (1976) or ACS Polym. Prepr., 21, 40 (1980), etc.)
In graft copolymerization through the conventional chain transfer reaction, a branch-forming monomer is subjected to polymerization in the presence of main carbon chain polymers. Therefore, the obtained graft polymer is uneven in the lengths and distribution of the branches. However, according to a newly proposed macromonomer method, a macromonomer can be produced by previously controlling properties such as molecular weight and its distribution, stereo-regularity, hydrophobic property and hydrophilic property. Such a macromonomer is used in polycondensation or polyaddition to produce a graft polymer, which is excellent as a method for designing the graft polymer molecule having a regulated molecular structure.
An example of the method for creating a new material by utilizing the macromonomer method is disclosed in the literature of “Chemistry and Industry of Macromonomer” (Yuya Yamashita, (1989), published by I. P. C.), in which a wide variety of macromonomers are proposed.
Meanwhile, several attempts to utilize butene oligomer derivatives as macromonomers have been done. However, in most butene oligomers, the main chain components are composed of isobutylene skeleton and they have functional groups at both α-terminals and ω-terminals. For example, J. P. Kennedy et al. disclose the production of a butene oligomer derivative having an isobutylene main chain and epoxy functional groups at both terminal ends, in a report of “Journal of Polymer Science”, Polymer Chemical Edition, vol. 20, p. 2809–2817 (1982).
However, it is apparent that the butene oligomer derivative like this having functional groups at both terminals is substantially different in molecular structure from the butene oligomer derivative having functional group on one side end of molecule according to the present invention.
As the butene oligomer which can be used as base polymer for developing butene oligomer derivatives, what is called “less reactive butene oligomer” has hitherto been produced using a catalyst of aluminum chloride or the like. In recent years, however, what is called “highly reactive butene oligomer” has been produced by changing its structure, especially the type of bonding olefin, by using various catalysts. This butene oligomer contains a large quantity of terminal vinylidene structure.
For example, in U.S. Pat. No. 4,152,499, a method for producing highly reactive butene oligomer is disclosed. Furthermore, it is also disclosed that a butene oligomer derivative having terminal group of succinic acid (hereinafter referred to as “succinic acid derivative”) can be produced at a high yield by reacting the butene oligomer with maleic anhydride.
As new derivatives utilizing the chemical reactivity of the highly reactive butene oligomer, there are several reports as well as the above-mentioned one on succinic acid derivative.
For example, there are carbonyl derivative in Japanese Patent No. 2,908,557; silyl derivative in Japanese Laid-Open Patent Publication No. H08-291,183; and oxo derivative and its modified compounds of monoamine derivatives in Japanese Patent No. 2,696,076.
As mentioned above, butene oligomer derivative as macromonomer that is capable of causing polycondensation/polyaddition at one side of terminals has never been disclosed.
It is, therefore, the object of the present invention to provide novel butene oligomer derivatives, as macromonomers, having functional groups of 1,4-butanediol at terminal ends, which macromonomer can be subjected to polycondensation and polyaddition.